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Chemical Structure| 13737-05-8 Chemical Structure| 13737-05-8

Structure of 13737-05-8

Chemical Structure| 13737-05-8

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Product Details of [ 13737-05-8 ]

CAS No. :13737-05-8
Formula : C8H13NSn
M.W : 241.91
SMILES Code : C[Sn](C)(C)C1=NC=CC=C1
MDL No. :MFCD01631312

Safety of [ 13737-05-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H300+H310+H330-H315-H319-H410-H227
Precautionary Statements:P501-P273-P260-P270-P262-P210-P271-P264-P280-P284-P370+P378-P391-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P310-P304+P340+P310-P403+P233-P403+P235-P405
Class:6.1
UN#:2788
Packing Group:

Application In Synthesis of [ 13737-05-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 13737-05-8 ]

[ 13737-05-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 13737-05-8 ]
  • [ 160539-04-8 ]
  • 2
  • [ 13737-05-8 ]
  • [ 232275-53-5 ]
  • 2,6-dichloro-4-(pyridin-2-yl)benzaldehyde [ No CAS ]
  • 2-chloro-4-(pyridin-2-yl)benzaldehyde [ No CAS ]
  • 3
  • [ 13737-05-8 ]
  • [ 232275-53-5 ]
  • methyl 2,6-dichloro-4-(pyridin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.5% With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 20 - 100℃; for 66.0h;Sealed tube; Inert atmosphere; In a sealed tube, <strong>[232275-53-5]methyl 4-bromo-2,6-dichlorobenzoate</strong>both (3.18 g,11.2 mmol) and 2-(trimethylstannyl)pyridine (1.94 ml, 11.2 mmol) and tetrakis(triphenyl phosphine)palladium (647.1 mg, 0.56 mmol) are suspended in DMF (25 mL). The mixture was degased with argon for 10 mm heated to 100 C for 18 hours, and then at room temperature. After 48 h the reaction was diluted with EtOAc and washed with KF (3 g in 50 mL water) andbrine (3x) and dried over Na2504, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (0% to 20% EtOAc/ hexanes) to afford methyl 2,6-dichloro-4-(pyridin-2-yl)benzoate (1.5 g, 47.5%). This material was dissolved in THF (25mL), cooled to 0 C, then lithium aluminum hydride (0.4 g, 10.63 mmol) was added slowly, after the addition was completed, the reaction mixture was warmed up slowly to roomtemperature and stirred for 1 h, then cooled back to 0 C added water (500 uL) slowly (vigorous gas evolution), followed by NaOH (2 M, 500 uL) then water (1500 uL). The slurry was stirred at room temperature. After 1 h, Na2504 was added, and then the mixture was filtered through Celite. The solid was rinsed with Et20 (200 mL), and the filtrate was concentrated under reduced pressure, the residue was diluted with EtOAc and washed with water then dried overNa2504, filtered and concentrated under reduced pressure. The cmde residue (1.5 g, 5.9 mmol) was combined with pyridinium chlorochromate (1.91 g, 8.85 mmol) and Celite (700 mg, 7mmol), DCM (10 mL) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction was filtered through a Celite frit with a small plug of silica, and rinsed several times with DCM/EtOAc, and then the filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography toafford P24 (392 mg, 26.3%). MS (ESI) mlz 252.0 [M+Hj . 1H NMR (400 MHz, Chloroformd) ö 10.54 (s, 1H), 8.74 (ddd, J = 4.8, 1.8, 0.9 Hz, 1H), 8.06 (s, 2H), 7.83 (ddd, J = 8.0, 7.4, 1.8 Hz, 1H), 7.77 (dt, J = 8.0, 1.1 Hz, 1H), 7.36 (ddd, J = 7.4, 4.8, 1.2 Hz, 1H) and P25 (195 mg, 15.2%). MS (ESI) m/z 218.1 [M+Hj . 1H NMR (400 MHz, Chloroform-d) ö 10.52 (d, J = 0.8 Hz, 1H), 8.74 (ddd, J = 4.8, 1.7, 1.0 Hz, 1H), 8.17 (dd, J = 1.6, 0.5 Hz, 1H), 8.07 - 7.95 (m, 2H),7.91 - 7.75 (m, 2H), 7.39 - 7.29 (m, 1H).
 

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